Milpitas city manager Tom Williams remains on paid leave as auditors investigate allegations that he spent public money on personal legal fees. But records obtained by San Jose Inside indicate that the $37,000 he charged to taxpayers this past April wasn’t the first time he misused city funds or signed off on questionable expenses.

A review of hundreds of pages of contracts found that Williams once hired a private eye to spy on a firefighter he suspected of faking an injury. But the $13,500 bill to hire investigator Ed Piggins was all for naught. The firefighter—veteran city employee Melvin Vaughn—suffered from legitimate back problems that required surgery. Vaughn sued the city, which shelled out $122,000 to settle the case in 2013.

Another deal authorized by Williams that’s raising eyebrows at City Hall is a $10,000-a-month contract with Forest Consulting, a lobbying firm run by Rich De La Rosa.

The contract, which cost the city at least $80,000 from 2015 to last year, described consulting services in unusually vague terms: “government affairs, analysis, strategic planning services and public communications.”

Several sources who spoke to San Jose Inside called the deal suspicious. Cities may hire lobbyists to advocate for local interests at the federal and state level, but it’s unclear why De La Rosa’s firm was needed if his responsibilities were strictly local. De La Rosa didn’t respond to a request for comment. Neither did Williams’ attorney, Claire Cochran, or the city’s outsourced legal counsel, Chris Diaz, who first alleged Williams had broken the law.

More problematic than the questionable contracts, however, are the legal expenses, which largely stem from Williams’ own personal conflicts.

On April 7, 2015, the city manager hired a Danville-based law firm—Gagen, McCoy, McMahon & Koss—to deal with a personnel complaint filed against him by the city’s former planning director, Steve McHarris. The agreement—rubber-stamped by Williams’ secretary, Rachelle Currie—fell a dollar below Williams’ signing authority: $19,999.

It’s unclear if Williams reimbursed the city for the money he charged to defend himself against the McHarris complaint, which accused the notoriously hotheaded city manager of hostility at work and unethical conduct with developers.

Records also show that a month later, in May 2015, the City Council upped Williams’ contract authority to $100,000. When Williams hired Ad Astra Law Group for $37,000 this year to send a cease-and-desist letter to Mayor Rich Tran and sue the city, Metro Silicon Valley (San Jose Inside’s parent newspaper) and the Milpitas Post, the council didn’t have to sign off on the expenses.

It wasn’t until San Jose Inside published that letter with the name of the law firm that city-hired auditors realized Ad Astra was hired to deal with Williams’ private legal conflicts. The city’s attorney warned Williams that the charge—even if it was reimbursed—constituted a violation of city policy and could lead to felony charges. The Santa Clara County District Attorney’s Office has confirmed it is monitoring the situation.